Acetic Acid → Tert-butyl [2-(benzylthio)-3-oxopropyl]carbamate

HRID 2239026Notes

Reaction equation

HRID 2239026 reaction equation
[CH2:1]([S:8][CH:9]([CH:19](OC)[O:20]C)[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>O1CCCC1.O>[CH2:1]([S:8][CH:9]([CH:19]=[O:20])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59136115Tert-butyl [2-(benzylthio)-3,3-dimethoxypropyl]carbamate

Product 1

HCID 59136000Tert-butyl [2-(benzylthio)-3-oxopropyl]carbamateYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl [2-(benzylthio)-3,3-dimethoxypropyl]carbamate (9.4 g) was dissolved in tetrahydrofuran (50 mL) and water (50 mL), and acetic acid (100 mL) was added. The reaction mixture was stirred overnight at 50° C., and concentrated, and the residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated brine, dried over sodium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give the title compound (5.35 g, yield 66%) as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (1:19).

Workup

  1. concentrationconcentrated
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-103d5f3ffeaa4e0dbb351c8b93a80905
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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